GB1016372A - Improvements in or relating to 17-esters of the androstane or estrane series - Google Patents

Improvements in or relating to 17-esters of the androstane or estrane series

Info

Publication number
GB1016372A
GB1016372A GB7087/63A GB708763A GB1016372A GB 1016372 A GB1016372 A GB 1016372A GB 7087/63 A GB7087/63 A GB 7087/63A GB 708763 A GB708763 A GB 708763A GB 1016372 A GB1016372 A GB 1016372A
Authority
GB
United Kingdom
Prior art keywords
group
prepared
chloride
esters
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB7087/63A
Inventor
Poul Borrevang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novo Terapeutisk Laboratorium AS
Original Assignee
Novo Terapeutisk Laboratorium AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novo Terapeutisk Laboratorium AS filed Critical Novo Terapeutisk Laboratorium AS
Priority to GB7087/63A priority Critical patent/GB1016372A/en
Priority to US334020A priority patent/US3238232A/en
Priority to DK69064AA priority patent/DK108859C/en
Priority to NO64152036A priority patent/NO123942B/no
Priority to NL6401565A priority patent/NL6401565A/xx
Priority to CH201764A priority patent/CH464185A/en
Priority to FI0334/64A priority patent/FI41649B/fi
Priority to AT146064A priority patent/AT257066B/en
Priority to FR964593A priority patent/FR3953M/fr
Priority to DEN24485A priority patent/DE1225637B/en
Priority to BE644173D priority patent/BE644173A/xx
Priority to SE2176/64A priority patent/SE315887B/xx
Publication of GB1016372A publication Critical patent/GB1016372A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Storage Of Web-Like Or Filamentary Materials (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1016372/C2/1> wherein the dotted line in ring A denotes the optional presence of double bonds, R1 represents a hydrogen atom or a methyl group, R2 represents two hydrogen atoms when a D 4 double bond is absent, or a hydrogen or chlorine atom or a hydroxyl group when a D 4 double bond is present, R3 represents a hydrogen atom or an alkyl group preferably having less than six carbon atoms, R4 represents two hydrogen atoms or one hydrogen atom with an a -methyl group, and X represents a chlorine atom or the group -OR in which R represents an alkyl, alkenyl, cycloalkyl, aryl, halo-substituted aryl, aralkyl, alkaryl, alkoxyaryl, aryloxy alkyl or heterocyclic radical. The compounds may be prepared by direct acylation of a steroid compound having a hydroxy group in the 17b position with chlorosulphonylacetyl chloride in an inert solvent to give the sulphonyl chloride. The sulphonate esters may be prepared by reaction of the sulphonyl chloride so produced with an alcohol or directly by addition of an alcohol during the acylation. The sulphoacetates may be prepared from 3,17-androstenediones by protecting the D 4-3-keto position, reducing the 17-keto group and reacting with chlorosulphonyl acetyl chloride. Esters of testosterone-17-sulphoacetate may be prepared by treating testosterone with a Grignard reagent and reacting the resulting 17-halomagnesium compound with chlorosulphonylacetyl chloride and an alcohol. Therapeutic compositions with anabolic and androgenic properties, in the form of oil solutions or aqueous suspensions for parenteral administration, contain esters of androstaneand estrane-17-sulphoacetates of the above general formula.
GB7087/63A 1963-02-21 1963-02-21 Improvements in or relating to 17-esters of the androstane or estrane series Expired GB1016372A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB7087/63A GB1016372A (en) 1963-02-21 1963-02-21 Improvements in or relating to 17-esters of the androstane or estrane series
US334020A US3238232A (en) 1963-02-21 1963-12-27 Esters of 17-beta-hydroxy-androstanes and 17-beta-hydroxy-estranes
DK69064AA DK108859C (en) 1963-02-21 1964-02-12 Process for the preparation of esters of sulfoacetates of the androstane and estran series.
NO64152036A NO123942B (en) 1963-02-21 1964-02-17
NL6401565A NL6401565A (en) 1963-02-21 1964-02-20
CH201764A CH464185A (en) 1963-02-21 1964-02-20 Method of making steroids
FI0334/64A FI41649B (en) 1963-02-21 1964-02-20
AT146064A AT257066B (en) 1963-02-21 1964-02-20 Process for the production of new steroid compounds of the androstane and estran series
FR964593A FR3953M (en) 1963-02-21 1964-02-21
DEN24485A DE1225637B (en) 1963-02-21 1964-02-21 Process for the production of steroid 17beta-sulfoacetate esters of the androstane and oestrane series
BE644173D BE644173A (en) 1963-02-21 1964-02-21
SE2176/64A SE315887B (en) 1963-02-21 1964-02-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7087/63A GB1016372A (en) 1963-02-21 1963-02-21 Improvements in or relating to 17-esters of the androstane or estrane series

Publications (1)

Publication Number Publication Date
GB1016372A true GB1016372A (en) 1966-01-12

Family

ID=9826365

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7087/63A Expired GB1016372A (en) 1963-02-21 1963-02-21 Improvements in or relating to 17-esters of the androstane or estrane series

Country Status (12)

Country Link
US (1) US3238232A (en)
AT (1) AT257066B (en)
BE (1) BE644173A (en)
CH (1) CH464185A (en)
DE (1) DE1225637B (en)
DK (1) DK108859C (en)
FI (1) FI41649B (en)
FR (1) FR3953M (en)
GB (1) GB1016372A (en)
NL (1) NL6401565A (en)
NO (1) NO123942B (en)
SE (1) SE315887B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR6576M (en) * 1965-10-11 1968-12-30

Also Published As

Publication number Publication date
BE644173A (en) 1964-08-21
SE315887B (en) 1969-10-13
FI41649B (en) 1969-09-30
FR3953M (en) 1966-02-28
NO123942B (en) 1972-02-07
CH464185A (en) 1968-10-31
DK108859C (en) 1968-02-19
NL6401565A (en) 1964-08-24
US3238232A (en) 1966-03-01
AT257066B (en) 1967-09-25
DE1225637B (en) 1966-09-29
DE1225637C2 (en) 1967-04-13

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